Triethylamine → (3R,4S)-4-[(Methylsulfonyl)oxy]tetrahydro-3-furanyl methanesulfonate
Reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[O:6]1[CH2:10][C@H:9]([OH:11])[C@H:8]([OH:12])[CH2:7]1.CCN(CC)CC>C(Cl)Cl>[CH3:1][S:2]([O:12][C@H:8]1[C@@H:9]([O:11][S:2]([CH3:1])(=[O:4])=[O:3])[CH2:10][O:6][CH2:7]1)(=[O:4])=[O:3]Participants
5
Conditions
- Temperature
- 0 °C
Procedure
Methanesulfonyl chloride (1.642 mL, 21.13 mmol) in DCM (5 mL) was added to a solution of (3R,4S)-tetrahydrofuran-3,4-diol (0.787 mL, 9.61 mmol) and Et3N (4.05 mL, 28.8 mmol) in DCM (10 mL) at 0° C. After stirring at 0° C. for 1 h, the mixture was diluted with DCM. The organic layer was washed with saturated aqueous NaHCO3, dried, and concentrated in vacuo to give the title compound as a yellowish white solid (2.5 g, 100%). 1H NMR (400 MHz, CDCl3) δ ppm 3.09-3.20 (m, 6H), 3.90-4.07 (m, 2H), 4.10-4.22 (m, 2H), 5.19 (ddd, J=5.31, 3.54, 1.77 Hz, 2H).
Workup
- washThe organic layer was washed with saturated aqueous NaHCO3
- customdried
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-94f0c967c97a470989cfe7f6188faee1
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181255B2
Reaction notes
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